HCID 10634805, compound → HCID 10844747, compound

HRID 2061346Notes

Reaction equation

HRID 2061346 reaction equation
C([O:3][CH:4](OCC)[CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:8]=1[CH:9]=O)C>C(O)(=O)C>[F:15][C:12]1[CH:13]=[CH:14][C:7]2[O:6][C:5]([CH:4]=[O:3])=[CH:9][C:8]=2[CH:11]=1

Participants

3

Reactant 1

HCID 10634805HCID 10634805, compound

Product 1

HCID 10844747HCID 10844747, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred solution of 12 (300 mg, 4.0 mmol) in acetic acid (10 mL) was refluxed for 24 h. After cooling, the solution was evaporated to dryness. The crude product was adsorbed on silica gel and purified by flash chromatography, eluting with hexane/EtOAc (4:1) to give the 13 (180 mg, 94%) as a white solid, 1H NMR (500 MHz, CDCl3): δ: 9.89 (1H, s, CHO), 7.57 (2H, m, ArH), 7.41 (1H, d, J=7.20 Hz), 7.26 (1H, d, J=6.94 Hz, H-4). 13C NMR CDEPT 135, (500 MHz, CDCl3): δ: 179.74 (CHO), 117.73 (C-3), 117.25 (C-7), 113.81 (C-6), 108.68 (C-4).

Workup

  1. temperatureAfter cooling
  2. customthe solution was evaporated to dryness
  3. custompurified by flash chromatography
  4. washeluting with hexane/EtOAc (4:1)

Sources & evidence

ORD record
ord-af0afb9a76be4537ab379dc816b2b2f4
Source dataset
uspto-grants-2012_10
Patent number
US08283340B2

Reaction notes

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